In their book, Practical Wisdom: The Right Way to Do the Right Thing, Barry Schwartz and Kenneth Sharpe highlight the task of sentencing a convicted criminal as quintessentially calling for practical wisdom. Wisdom, they argue, is not a transcendent state to be achieved by mystical means but a skill that must be learned and improved by practice, trial, and error. It is grounded in empathy, which is the cognitive ability “to imagine what someone else is thinking and feeling.” A person’s capacity for wisdom can be stunted by rote adherence to inflexible rules or by carrots and sticks that replace good character with a reward system. Professor Benjamin Barton’s new Article argues that the rarified and insular biographies of the current justices of the Supreme Court are ill-suited for developing practical wisdom.